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We present here synthesis and crystal structure of a neutral IrIII complex, [Ir(C19H13N2)2(C15H11O2)]·2CH2Cl2 or [Ir(C^N)2O^O]·2CH2Cl2, where C^N is 1,2-diphenyl-1H-benzimidazole and O^O is 2-benzoyl-1-phenyl­ethenolate. The coordination sphere of the IrIII atom, located on a twofold rotation axis, is that of a slighlty distorted C2N2O2 octa­hedron, with the N atoms in a trans configuration. In the crystal, complex mol­ecules assemble through weak C—H...π inter­actions in the range 2.699 (3)–2.892 (3) Å. The solvent CH2Cl2 molecules reside in channels aligned along the a axis and are connected to the complex molecules by C—H...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314616019155/wm4034sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314616019155/wm4034Isup2.hkl
Contains datablock I

CCDC reference: 1517541

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.018
  • wR factor = 0.043
  • Data-to-parameter ratio = 20.6

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.31 Report PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors of C31 Check
Alert level G PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large 6.30 Why ? PLAT432_ALERT_2_G Short Inter X...Y Contact Cl2 .. C11 .. 3.24 Ang. PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min) 1 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 2 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 9 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(2-Benzoyl-1-phenylethenolato-κ2O,O')bis[2-(1-phenyl-1H-benzimidazol-2-yl)phenyl-κC1]iridium(III) dichloromethane disolvate top
Crystal data top
[Ir(C19H13N2)2(C15H11O2)]·2CH2Cl2Dx = 1.605 Mg m3
Mr = 1123.92Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Aba2Cell parameters from 9873 reflections
a = 13.9159 (7) Åθ = 2.2–30.5°
b = 25.5352 (12) ŵ = 3.15 mm1
c = 13.0898 (6) ÅT = 150 K
V = 4651.4 (4) Å3Plate, orange
Z = 40.40 × 0.25 × 0.15 mm
F(000) = 2240
Data collection top
Bruker SMART APEXII
diffractometer
5029 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
ω scansθmax = 29.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1818
k = 3434
21901 measured reflectionsl = 1717
6169 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.018 w = 1/[σ2(Fo2) + (0.0163P)2 + 6.3016P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.043(Δ/σ)max < 0.001
S = 1.07Δρmax = 1.07 e Å3
6169 reflectionsΔρmin = 0.46 e Å3
299 parametersAbsolute structure: Flack x determined using 2201 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute structure parameter: 0.007 (3)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ir10.00000.00000.87622 (4)0.01596 (4)
O10.0422 (2)0.05472 (12)0.7569 (2)0.0202 (6)
N10.12555 (19)0.04069 (10)0.8901 (2)0.0173 (6)
N20.2133 (2)0.10159 (12)0.9688 (2)0.0202 (6)
C10.0377 (3)0.05237 (16)0.9825 (3)0.0169 (8)
C20.1284 (3)0.06017 (15)1.0264 (3)0.0206 (7)
H6A0.17990.03781.00700.025*
C30.1456 (3)0.09984 (15)1.0979 (3)0.0250 (8)
H5A0.20840.10441.12500.030*
C40.0721 (3)0.13256 (18)1.1296 (3)0.0261 (10)
H4A0.08390.15861.17980.031*
C50.0197 (3)0.12704 (16)1.0873 (3)0.0238 (8)
H3A0.07040.14961.10760.029*
C60.0357 (3)0.08776 (15)1.0147 (3)0.0199 (7)
C70.1252 (3)0.07847 (14)0.9607 (3)0.0187 (7)
C80.2463 (3)0.14125 (14)1.0383 (3)0.0209 (7)
C90.2713 (3)0.12733 (17)1.1363 (3)0.0312 (10)
H15A0.26270.09231.15910.037*
C100.3093 (3)0.16477 (19)1.2019 (3)0.0385 (11)
H16A0.32610.15561.26990.046*
C110.3226 (3)0.21529 (18)1.1675 (4)0.0346 (10)
H17A0.34920.24091.21190.042*
C120.2977 (4)0.22885 (18)1.0693 (4)0.0403 (11)
H19A0.30650.26381.04640.048*
C130.2600 (3)0.19165 (17)1.0038 (3)0.0360 (10)
H18A0.24370.20080.93560.043*
C140.2745 (3)0.07636 (14)0.8998 (2)0.0208 (8)
C150.3710 (2)0.08408 (13)0.8788 (4)0.0246 (6)
H12A0.40770.11020.91270.029*
C160.4109 (3)0.05164 (17)0.8058 (3)0.0271 (8)
H11A0.47690.05550.78890.033*
C170.3568 (3)0.01333 (15)0.7562 (3)0.0244 (8)
H10A0.38700.00790.70600.029*
C180.2600 (3)0.00515 (14)0.7776 (3)0.0219 (7)
H9A0.22370.02130.74410.026*
C190.2191 (2)0.03793 (14)0.8509 (2)0.0179 (7)
C200.00000.00000.6161 (4)0.0263 (11)
H21A0.00000.00000.54350.032*
C210.0349 (3)0.04551 (14)0.6622 (3)0.0194 (7)
C220.0652 (3)0.08839 (15)0.5905 (3)0.0213 (7)
C230.0429 (3)0.13971 (18)0.6134 (3)0.0290 (10)
H24A0.01130.14780.67590.035*
C240.0662 (4)0.17976 (18)0.5457 (4)0.0381 (11)
H25A0.04930.21490.56140.046*
C250.1137 (3)0.16867 (17)0.4558 (3)0.0362 (10)
H26A0.13010.19610.41000.043*
C260.1373 (3)0.11718 (17)0.4325 (3)0.0294 (9)
H27A0.17080.10940.37110.035*
C270.1123 (3)0.07730 (16)0.4986 (3)0.0243 (8)
H28A0.12720.04210.48150.029*
C310.1018 (3)0.32965 (17)0.3649 (4)0.0386 (11)
H31A0.08380.36340.33310.046*
H31B0.12830.33700.43360.046*
Cl10.00094 (11)0.28980 (5)0.3765 (3)0.0586 (3)
Cl20.18966 (10)0.29873 (7)0.28987 (11)0.0620 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ir10.01740 (7)0.01518 (7)0.01531 (6)0.00053 (8)0.0000.000
O10.0239 (16)0.0183 (16)0.0183 (13)0.0011 (12)0.0007 (12)0.0014 (12)
N10.0189 (12)0.0176 (13)0.0153 (17)0.0023 (10)0.0004 (11)0.0010 (12)
N20.0207 (15)0.0215 (15)0.0184 (14)0.0016 (12)0.0006 (12)0.0039 (12)
C10.023 (2)0.015 (2)0.0127 (16)0.0016 (16)0.0002 (15)0.0030 (14)
C20.0211 (17)0.0209 (18)0.0200 (17)0.0011 (14)0.0008 (14)0.0009 (14)
C30.0244 (19)0.026 (2)0.0248 (19)0.0071 (15)0.0053 (15)0.0015 (15)
C40.029 (2)0.029 (2)0.0205 (18)0.0084 (17)0.0044 (16)0.0054 (16)
C50.025 (2)0.025 (2)0.0208 (17)0.0004 (14)0.0028 (14)0.0046 (15)
C60.0203 (16)0.0210 (19)0.0183 (17)0.0030 (15)0.0001 (14)0.0001 (14)
C70.0212 (17)0.0172 (17)0.0177 (17)0.0007 (13)0.0001 (13)0.0006 (14)
C80.0178 (16)0.0234 (18)0.0214 (17)0.0011 (14)0.0006 (13)0.0050 (15)
C90.039 (3)0.030 (2)0.025 (2)0.0131 (17)0.0054 (19)0.0043 (17)
C100.045 (3)0.050 (3)0.0197 (19)0.016 (2)0.0026 (18)0.0027 (19)
C110.035 (2)0.034 (2)0.035 (2)0.0056 (18)0.0003 (19)0.0153 (19)
C120.056 (3)0.019 (2)0.047 (3)0.003 (2)0.011 (2)0.0046 (19)
C130.048 (3)0.025 (2)0.034 (2)0.0034 (19)0.016 (2)0.0020 (18)
C140.0225 (17)0.0207 (17)0.019 (2)0.0036 (13)0.0003 (12)0.0006 (12)
C150.0214 (15)0.0263 (16)0.0261 (16)0.0036 (12)0.003 (2)0.003 (2)
C160.0193 (18)0.033 (2)0.029 (2)0.0011 (16)0.0023 (15)0.0007 (17)
C170.0247 (18)0.026 (2)0.0222 (17)0.0053 (14)0.0022 (15)0.0028 (14)
C180.0244 (17)0.0218 (19)0.0195 (15)0.0015 (15)0.0016 (13)0.0014 (15)
C190.0184 (16)0.0188 (16)0.0166 (17)0.0016 (13)0.0006 (11)0.0004 (12)
C200.034 (3)0.028 (3)0.017 (2)0.008 (3)0.0000.000
C210.0167 (15)0.0215 (18)0.0202 (16)0.0004 (14)0.0001 (14)0.0021 (14)
C220.0217 (17)0.0227 (19)0.0196 (16)0.0022 (14)0.0011 (14)0.0035 (14)
C230.035 (2)0.026 (2)0.026 (2)0.0007 (19)0.0047 (19)0.0026 (18)
C240.055 (3)0.021 (2)0.038 (2)0.0029 (19)0.007 (2)0.0073 (18)
C250.045 (3)0.028 (2)0.036 (2)0.0024 (19)0.006 (2)0.0135 (19)
C260.032 (2)0.034 (2)0.0227 (19)0.0030 (18)0.0063 (16)0.0050 (16)
C270.0248 (19)0.0247 (19)0.0235 (19)0.0007 (15)0.0011 (15)0.0016 (15)
C310.049 (2)0.033 (2)0.034 (3)0.0042 (17)0.008 (2)0.007 (2)
Cl10.0683 (7)0.0556 (6)0.0518 (6)0.0168 (7)0.0125 (7)0.0098 (18)
Cl20.0531 (8)0.0838 (11)0.0490 (7)0.0266 (8)0.0111 (6)0.0246 (7)
Geometric parameters (Å, º) top
Ir1—C1i1.999 (4)C12—H19A0.9500
Ir1—C11.999 (4)C13—H18A0.9500
Ir1—N1i2.041 (3)C14—C151.386 (5)
Ir1—N12.041 (3)C14—C191.402 (5)
Ir1—O1i2.176 (3)C15—C161.381 (6)
Ir1—O12.176 (3)C15—H12A0.9500
O1—C211.267 (5)C16—C171.395 (6)
N1—C71.337 (4)C16—H11A0.9500
N1—C191.400 (4)C17—C181.392 (5)
N2—C71.365 (5)C17—H10A0.9500
N2—C141.398 (4)C18—C191.395 (5)
N2—C81.436 (5)C18—H9A0.9500
C1—C21.402 (6)C20—C21i1.397 (4)
C1—C61.427 (6)C20—C211.397 (4)
C2—C31.400 (5)C20—H21A0.9500
C2—H6A0.9500C21—C221.502 (5)
C3—C41.385 (6)C22—C231.380 (6)
C3—H5A0.9500C22—C271.400 (5)
C4—C51.399 (5)C23—C241.392 (6)
C4—H4A0.9500C23—H24A0.9500
C5—C61.400 (5)C24—C251.379 (6)
C5—H3A0.9500C24—H25A0.9500
C6—C71.451 (5)C25—C261.389 (6)
C8—C91.377 (5)C25—H26A0.9500
C8—C131.377 (5)C26—C271.380 (5)
C9—C101.389 (6)C26—H27A0.9500
C9—H15A0.9500C27—H28A0.9500
C10—C111.379 (7)C31—Cl21.755 (5)
C10—H16A0.9500C31—Cl11.762 (5)
C11—C121.375 (7)C31—H31A0.9900
C11—H17A0.9500C31—H31B0.9900
C12—C131.383 (6)
C1i—Ir1—C191.9 (2)C11—C12—C13120.1 (4)
C1i—Ir1—N1i79.76 (15)C11—C12—H19A119.9
C1—Ir1—N1i93.11 (15)C13—C12—H19A119.9
C1i—Ir1—N193.11 (15)C8—C13—C12119.4 (4)
C1—Ir1—N179.76 (15)C8—C13—H18A120.3
N1i—Ir1—N1169.81 (18)C12—C13—H18A120.3
C1i—Ir1—O1i177.96 (17)C15—C14—N2130.7 (4)
C1—Ir1—O1i89.94 (10)C15—C14—C19122.8 (3)
N1i—Ir1—O1i99.17 (12)N2—C14—C19106.4 (3)
N1—Ir1—O1i88.17 (12)C16—C15—C14116.2 (4)
C1i—Ir1—O189.94 (10)C16—C15—H12A121.9
C1—Ir1—O1177.96 (17)C14—C15—H12A121.9
N1i—Ir1—O188.17 (12)C15—C16—C17121.7 (4)
N1—Ir1—O199.17 (12)C15—C16—H11A119.1
O1i—Ir1—O188.29 (16)C17—C16—H11A119.1
C21—O1—Ir1124.2 (3)C18—C17—C16122.3 (4)
C7—N1—C19107.0 (3)C18—C17—H10A118.9
C7—N1—Ir1115.2 (2)C16—C17—H10A118.9
C19—N1—Ir1137.5 (2)C17—C18—C19116.3 (3)
C7—N2—C14107.3 (3)C17—C18—H9A121.8
C7—N2—C8129.8 (3)C19—C18—H9A121.8
C14—N2—C8122.6 (3)C18—C19—N1131.4 (3)
C2—C1—C6115.7 (4)C18—C19—C14120.6 (3)
C2—C1—Ir1128.1 (3)N1—C19—C14108.0 (3)
C6—C1—Ir1116.2 (3)C21i—C20—C21128.8 (5)
C3—C2—C1122.1 (4)C21i—C20—H21A115.6
C3—C2—H6A119.0C21—C20—H21A115.6
C1—C2—H6A119.0O1—C21—C20127.3 (4)
C4—C3—C2120.7 (4)O1—C21—C22117.0 (3)
C4—C3—H5A119.6C20—C21—C22115.8 (3)
C2—C3—H5A119.6C23—C22—C27119.0 (4)
C3—C4—C5119.7 (4)C23—C22—C21119.5 (4)
C3—C4—H4A120.2C27—C22—C21121.4 (3)
C5—C4—H4A120.2C22—C23—C24120.4 (4)
C4—C5—C6119.1 (4)C22—C23—H24A119.8
C4—C5—H3A120.4C24—C23—H24A119.8
C6—C5—H3A120.4C25—C24—C23120.3 (4)
C5—C6—C1122.7 (4)C25—C24—H25A119.9
C5—C6—C7125.8 (4)C23—C24—H25A119.9
C1—C6—C7111.5 (3)C24—C25—C26119.7 (4)
N1—C7—N2111.2 (3)C24—C25—H26A120.2
N1—C7—C6117.3 (3)C26—C25—H26A120.2
N2—C7—C6131.5 (3)C27—C26—C25120.1 (4)
C9—C8—C13120.8 (4)C27—C26—H27A119.9
C9—C8—N2119.3 (3)C25—C26—H27A119.9
C13—C8—N2119.7 (3)C26—C27—C22120.5 (4)
C8—C9—C10119.6 (4)C26—C27—H28A119.8
C8—C9—H15A120.2C22—C27—H28A119.8
C10—C9—H15A120.2Cl2—C31—Cl1110.7 (3)
C11—C10—C9119.6 (4)Cl2—C31—H31A109.5
C11—C10—H16A120.2Cl1—C31—H31A109.5
C9—C10—H16A120.2Cl2—C31—H31B109.5
C12—C11—C10120.5 (4)Cl1—C31—H31B109.5
C12—C11—H17A119.8H31A—C31—H31B108.1
C10—C11—H17A119.8
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C31—H31A···O1ii0.992.393.377 (6)179
Symmetry code: (ii) x, y+1/2, z1/2.
 

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